Photoswitchable Phosphonate–Fullerene Hybrids with Cholinesterase Activity

Modern progress in photopharmocology calls for new generation of compounds joining bioactivity, photoswitchable properties and high selectivity of response to light wavelength. Introduced here, phosphonate–fullerene hybrids are the first representatives of such compounds. Phosphonate–fullerene hybri...

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Bibliographic Details
Published in:Photochemistry and photobiology 2023-05, Vol.99 (3), p.929-935
Main Authors: Kolesnikov, Ilya, Mamonova, Daria, Pankin, Dmitrii, Bikbaeva, Gulia, Khokhlova, Anastasia, Pilip, Anna, Egorova, Anastasia, Zigel, Vladislav, Manshina, Alina
Format: Article
Language:English
Subjects:
Biological activity
Butyrylcholinesterase
Cholinesterase
Electrical measurement
Fullerenes
Fullerenes - chemistry
Hybrids
Irradiation
Lasers
Light
Light effects
Neurotoxins
Organophosphates
Phosphonates
Spectrum Analysis
Toxins
Wavelength
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Summary:Modern progress in photopharmocology calls for new generation of compounds joining bioactivity, photoswitchable properties and high selectivity of response to light wavelength. Introduced here, phosphonate–fullerene hybrids are the first representatives of such compounds. Phosphonate–fullerene hybrids were synthesized on a base of fullerene C60 and organophosphates with the function of photoswitchable cholinesterase activity—phosphorylated thiazolotriazole and aminomalonate compounds and studied with FTIR, UV–VIS spectroscopy and IPC‐micro neurotoxin amperometric analysis. As a result of spectroscopic and bioactivity characterization, it was not only demonstrated butyrylcholinesterase (BuChE) inhibition increase in phosphonate–fullerene hybrids compared with pure phosphonates but also pronounced response of inhibition degree to laser irradiation of hybrids. It was found opposite behavior of hybrids as a result of laser irradiation—BuChE inhibition drop‐off for thiazolotriazole–fullerene and pronounced growth for aminomalonate–fullerene. The other remarkable peculiarity of presented phosphonate–fullerene hybrids is high selectivity of inhibition change degree to laser wavelength (266 or 325 nm). Phosphonate–fullerene hybrids with three simultaneous characteristics—bioactivity, photoinduce change of bioactivity, selectivity of inhibition change to laser wavelength.
ISSN:0031-8655
1751-1097
DOI:10.1111/php.13720